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Nickel-Catalyzed Double Bond Transposition of Alkenyl Boronates for in Situ syn-Selective Allylboration Reactions

Felicia Weber, Monika Ballmann, Corinna Kohlmeyer and Gerhard Hilt*

*Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße 4, D-35043 Marburg, Germany, Email: Hiltchemie.uni-marburg.de

F. Weber, M. Ballmann, C. Kohlmeyer, G. Hilt, Org. Lett., 2016, 18, 548-551.

DOI: 10.1021/acs.orglett.5b03585 (free Supporting Information)


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Abstract

A highly reactive nickel-catalyst system enables an in situ transposition of a homoallyl pinacol boronic ester to a Z-crotyl pinacol boronic ester, that reacts with various aldehydes to form syn-homoallylic alcohols in high diastereoselectivities. Also, the multiple transposition of pentenyl pinacol boronic ester was realized.

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Key Words

homoallylic alcohols


ID: J54-Y2016